Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes
Publication type: Journal Article
Publication date: 2005-12-02
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract
Regioselective Markovnikov-type addition of PhSH to alkynes (HCC-R) has been performed using easily available nickel complexes. The non-cata- lytic side reaction leading to anti-Markovnikov prod- ucts was suppressed by addition of g-terpinene to the catalytic system. The other side reaction leading to the bis(phenylthio)alkene was avoided by excluding phosphine and phosphite ligands from the catalytic system. It was found that catalytic amounts of Et3N significantly increased the yield and selectivity of the catalytic reaction. Under optimized conditions high product yields of 60 - 85% were obtained for var- ious alkynes (R ¼ n-C5H11 ,C H 2NMe2 ,C H 2OMe, CH2SPh, C6H11(OH), (CH2)3CN). The X-ray structure of one of the synthesized products is reported.
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Citations from 2024:
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GOST
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Ananikov V. P. et al. Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes // Advanced Synthesis and Catalysis. 2005. Vol. 347. No. 15. pp. 1993-2001.
GOST all authors (up to 50)
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Ananikov V. P., Malyshev D. A., Beletskaya I. P., Aleksandrov G. G., Eremenko I. L. Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes // Advanced Synthesis and Catalysis. 2005. Vol. 347. No. 15. pp. 1993-2001.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/adsc.200505168
UR - https://doi.org/10.1002/adsc.200505168
TI - Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes
T2 - Advanced Synthesis and Catalysis
AU - Ananikov, Valentine P.
AU - Malyshev, Denis A
AU - Beletskaya, Irina P.
AU - Aleksandrov, Grigory G.
AU - Eremenko, Igor L.
PY - 2005
DA - 2005/12/02
PB - Wiley
SP - 1993-2001
IS - 15
VL - 347
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2005_Ananikov,
author = {Valentine P. Ananikov and Denis A Malyshev and Irina P. Beletskaya and Grigory G. Aleksandrov and Igor L. Eremenko},
title = {Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes},
journal = {Advanced Synthesis and Catalysis},
year = {2005},
volume = {347},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/adsc.200505168},
number = {15},
pages = {1993--2001},
doi = {10.1002/adsc.200505168}
}
Cite this
MLA
Copy
Ananikov, Valentine P., et al. “Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes.” Advanced Synthesis and Catalysis, vol. 347, no. 15, Dec. 2005, pp. 1993-2001. https://doi.org/10.1002/adsc.200505168.